Production of resins from butadiene monoxide and from mixtures of butadiene monoxide and vinyl compounds



Patented Got. 9, 1951 UNITED STATES PATENT OFFICE POUNDS LouisSchmerling, Riverside, Ill., assignor to Universal Oil Products Company,Chicago, 111., a

corporation of Delaware No Drawing. Application November 13, 1950,

Serial No. 195,463

4 Claims.

This application is a continuation-in-part of my copending applicationSerial Number 632,288, filed December 1, 1945, and now abandoned.

This invention relates to a process for producing plastics and resins.More particularly, it relates to the formation of a resin by the thermaltreatment of a reaction mixture containing butadiene monoxide.

An object of this invention is to polymerize butadiene monoxide to forma resin.

Another object of this invention is to form a resin by thermallycopolymerizing butadiene monoxide and a vinyl compound.

One specific embodiment of this invention relates to a process whichcomprises thermally treating butadiene monoxide at a temperature of fromabout 150 to about 350 C. to form a resin.

Another embodiment of this invention relates to a process whichcomprises thermally treating butadiene monoxide at a temperature of fromabout 150 to about 350 C. in the presence of a vinyl compound selectedfrom the group consisting of vinyl chloride, vinyl acetate,acrylonitrile, butadiene, and styrene.

Butadiene monoxide, or 3,4-epoxy-1-butene, utilized in the process ofthis invention is an organic compound containing one oxygen atom and onedouble bond per molecule and having the formula:

Vinyl compounds which may be copob'merized with butadiene monoxideinclude particularly vinyl chloride, vinyl acetate, acrylonitrile,butadiene, and styrene.

My process for producing a resin is carried out by treating butadienemonoxide at a temperature of from about 150 to about 350 0. to effectpolymerization. Butadiene monoxide polymerizes with itself to form ahard, clear yellow resin, but it is sometimes desirable to copolymerizebutadiene monoxide with another vinyl compound selected from the groupconsisting of vinyl chloride, vinyl acetate, acrylonitrile, butadiene,styrene and alpha-methylstyrene, particularly since these vinylcompounds are generally less expensive thanthe butadiene monoxide. Also,the mixed polymer or copolymer resins so formed have some more desirableproperties for certain purposes than does the resin formed fromsubstantially pure butadiene monoxide. These different resins have lowsolubilities in organic solvents, particularly hydrocarbons andaccordingly are useful as surface coatings which are melted and appliedhot to the materials and articles to be coated.

My process may be carried out in either batch or continuous types ofoperation, the latter generally being preferable. An autoclave isutilizable in batch type polymerization runs for producing my resins,while the continuous type of treatment may utilize a tubular reactor,which may or may not contain a layer of a granular solid packingmaterial such as crushed porcelain, silica, firebrick, etc., or thereactor may be provided with bafiles or other mixing equipment. Thereaction mixture is then directed to suitable separating means in whichunconverted startin materials are separated from the desired reactionproduct and the former are recycled to the process.

The resins formed in this process are useful as surface coating agentsfor metals, wood, paper, etc. These resins may also be molded intofinished articles including fiat plates or sheets, toys, plastic-typedishes and the like. These resins may also be mixed with wood flour,diatomaceous earth and other solid diluents or spacing agents and theresultant mixtures may then be formed into various articles ofmanufacture. Some of the resinous materials of lower molecular weightwhich have the consistency of viscous liquids may be employed asplasticizers for other resins and plastics.

The following examples are given of results obtained in this process,although these data are not to be considered as limiting unduly thebroad scope of the invention.

Example I 25 grams of butadiene monoxide was sealed into a glass tubewhich was then inserted in a steel autoclave and heated therein at 250C. for 2 hours. After the autoclave and its contents had cooled to about25 C., the reaction mixture was removed therefrom and separated into ahard, yellow resin and a smaller amount of a viscous yellow liquid. Theresin so obtained was insoluble in higher hydrocarbons. It wasthermoplastic and could be molded into useful articles.

Example 11 A mixture of 50 grams of butadiene monoxide and 15 grams ofalpha-methylstyrene in a sealed tube was heated at 250 C. for fourhours. The product was a brittle clear amber thermoplastic resin whichcould be drawn into threads while hot, and also could be molded.

I claim as my invention:

1. A process for producing a resin which comprises heating3,4-epoxy-1-butene and a vinyl compound at a temperature of from about150 to about 350 C.

2. A resin formed by heating 3,4-epoxy-1- butene and a vinyl compound ata temperature of from about 150 to about 350 C.

3. A process for producing a resin which comprises heating3,4-epoxy-1-butene at a temperature of from about 150 to about 350 C.

4. A resin formed by heating 3,4-epoxy-1- butene at a temperature offrom about 150 to about 350 C.

LOUIS SCHMIRLING.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS OTHER REFERENCES Pummerer et al.: Berichte, 663,pp. 335-339 (1933).

1. A PROCESS FOR PRODUCING A RESIN WHICH COMPRISES HEATING3,4-EPOXY-1-BUTENE AND A VINYL COMPOUND AT A TEMPERATURE OF FROM ABOUT150* TO ABOUT 350* C.